Advertisement

Phenolic Lipids Synthesized by Type III Polyketide Synthases

  • Akimasa MiyanagaEmail author
  • Yasuo Ohnishi
Reference work entry
Part of the Handbook of Hydrocarbon and Lipid Microbiology book series (HHLM)

Abstract

Phenolic lipids, consisting of a polar aromatic ring and a hydrophobic alkyl chain, are distributed widely in bacteria, fungi, and plants, and they appear to play important roles in biological membranes. Here, recent studies of the biosynthesis of microbial and plant phenolic lipids are described. Phenolic lipids are biosynthesized by a combination of a fatty acid synthase and a type III polyketide synthase, which are responsible for synthesizing the alkyl chain and the aromatic ring, respectively.

References

  1. Austin MB, Noel JP (2003) The chalcone synthase superfamily of type III polyketide synthases. Nat Prod Rep 20:79–110CrossRefGoogle Scholar
  2. Awakawa T, Fujita N, Hayakawa M, Ohnishi Y, Horinouchi S (2011) Characterization of the biosynthesis gene cluster for alkyl-O-dihydrogeranyl-methoxyhydroquinones in Actinoplanes missouriensis. Chembiochem 12:439–448CrossRefGoogle Scholar
  3. Awakawa T, Sugai Y, Otsutomo K, Ren S, Masuda S, Katsuyama Y, Horinouchi S, Ohnishi Y (2013) 4-Hydroxy-3-methyl-6-(1-methyl-2-oxoalkyl)pyran-2-one synthesis by a type III polyketide synthase from Rhodospirillum centenum. Chembiochem 14:1006–1013CrossRefGoogle Scholar
  4. Baerson SR, Dayan FE, Rimando AM, Nanayakkara NP, Liu CJ, Schröder J, Fishbein M, Pan Z, Kagan IA, Pratt LH, Cordonnier-Pratt MM, Duke SO (2008) A functional genomics investigation of allelochemical biosynthesis in Sorghum bicolor root hairs. J Biol Chem 283:3231–3247CrossRefGoogle Scholar
  5. Brameyer S, Kresovic D, Bode HB, Heermann R (2015) Dialkylresorcinols as bacterial signaling molecules. Proc Natl Acad Sci U S A 112:572–577CrossRefGoogle Scholar
  6. Colpitts CC, Kim SS, Posehn SE, Jepson C, Kim SY, Wiedemann G, Reski R, Wee AGH, Douglas CJ, Suh DY (2011) PpASCL, a moss ortholog of anther-specific chalcone synthase-like enzymes, is a hydroxyalkylpyrone synthase involved in an evolutionarily conserved sporopollenin biosynthesis pathway. New Phytol 192:855–868CrossRefGoogle Scholar
  7. Cook D, Rimando AM, Clemente TE, Schröder J, Dayan FE, Nanayakkara NP, Pan Z, Noonan BP, Fishbein M, Abe I, Duke SO, Baerson SR (2010) Alkylresorcinol synthases expressed in Sorghum bicolor root hairs play an essential role in the biosynthesis of the allelopathic benzoquinone sorgoleone. Plant Cell 22:867–887CrossRefGoogle Scholar
  8. Dayan FE, Kagan IA, Rimando AM (2003) Elucidation of the biosynthetic pathway of the allelochemical sorgoleone using retrobiosynthetic NMR analysis. J Biol Chem 278:28607–28611CrossRefGoogle Scholar
  9. Dayan FE, Watson SB, Nanayakkara NP (2007) Biosynthesis of lipid resorcinols and benzoquinones in isolated secretory plant root hairs. J Exp Bot 58:3263–3272CrossRefGoogle Scholar
  10. Dayan FE, Rimando AM, Pan Z, Baerson SR, Gimsing AL, Duke SO (2010) Sorgoleone. Phytochemistry 71:1032–1039CrossRefGoogle Scholar
  11. de Azevedo SC, Kim SS, Koch S, Kienow L, Schneider K, McKim SM, Haughn GW, Kombrink E, Douglas CJ (2009) A novel fatty acyl-CoA synthetase is required for pollen development and sporopollenin biosynthesis in Arabidopsis. Plant Cell 21:507–525CrossRefGoogle Scholar
  12. Dobritsa AA, Shrestha J, Morant M, Pinot F, Matsuno M, Swanson R, Møller BL, Preuss D (2009) CYP704B1 is a long-chain fatty acid omega-hydroxylase essential for sporopollenin synthesis in pollen of Arabidopsis. Plant Physiol 151:574–589CrossRefGoogle Scholar
  13. Fuchs SW, Bozhüyük KA, Kresovic D, Grundmann F, Dill V, Brachmann AO, Waterfield NR, Bode HB (2013) Formation of 1,3-cyclohexanediones and resorcinols catalyzed by a widely occurring ketosynthase. Angew Chem Int Ed 52:4108–4112CrossRefGoogle Scholar
  14. Funa N, Ozawa H, Hirata A, Horinouchi S (2006) Phenolic lipid synthesis by type III polyketide synthases is essential for cyst formation in Azotobacter vinelandii. Proc Natl Acad Sci U S A 103:6356–6361CrossRefGoogle Scholar
  15. Funa N, Awakawa T, Horinouchi S (2007) Pentaketide resorcylic acid synthesis by type III polyketide synthase from Neurospora crassa. J Biol Chem 282:14476–14481CrossRefGoogle Scholar
  16. Funabashi M, Funa N, Horinouchi S (2008) Phenolic lipids synthesized by type III polyketide synthase confer penicillin resistance on Streptomyces griseus. J Biol Chem 283:13983–13991CrossRefGoogle Scholar
  17. Gellerman JL, Anderson WH, Schlenk H (1976) Synthesis of anacardic acids in seeds of Ginkgo biloba. Biochim Biophys Acta 431:16–21CrossRefGoogle Scholar
  18. Grienenberger E, Kim SS, Lallemand B, Geoffroy P, Heintz D, Souza Cde A, Heitz T, Douglas CJ, Legrand M (2010) Analysis of TETRAKETIDE α-PYRONE REDUCTASE function in Arabidopsis thaliana reveals a previously unknown, but conserved, biochemical pathway in sporopollenin monomer biosynthesis. Plant Cell 22:4067–4083CrossRefGoogle Scholar
  19. Hayashi T, Kitamura Y, Funa N, Ohnishi Y, Horinouchi S (2011) Fatty acyl-AMP ligase involvement in the production of alkylresorcylic acid by a Myxococcus xanthus type III polyketide synthase. Chembiochem 12:2166–2176CrossRefGoogle Scholar
  20. Jeya M, Kim TS, Tiwari MK, Li J, Zhao H, Lee JK (2012) The Botrytis cinerea type III polyketide synthase shows unprecedented high catalytic efficiency toward long chain acyl-CoAs. Mol BioSyst 8:2864–2867CrossRefGoogle Scholar
  21. Katsuyama Y, Ohnishi Y (2012) Type III polyketide synthases in microorganisms. Methods Enzymol 515:359–377CrossRefGoogle Scholar
  22. Kim SS, Grienenberger E, Lallemand B, Colpitts CC, Kim SY, Souza Cde A, Geoffroy P, Heintz D, Krahn D, Kaiser M, Kombrink E, Heitz T, Suh DY, Legrand M, Douglas CJ (2010) LAP6/POLYKETIDE SYNTHASE A and LAP5/POLYKETIDE SYNTHASE B encode hydroxyalkyl α-pyrone synthases required for pollen development and sporopollenin biosynthesis in Arabidopsis thaliana. Plant Cell 22:4045–4066CrossRefGoogle Scholar
  23. Kozubek A, Tyman JH (1999) Resorcinolic lipids, the natural non-isoprenoid phenolic amphiphiles and their biological activity. Chem Rev 99:1–26CrossRefGoogle Scholar
  24. Lin LP, Sadoff HL (1968) Encystment and polymer production by Azotobacter vinelandii in the presence of beta-hydroxybutyrate. J Bacteriol 95:2336–2343PubMedPubMedCentralGoogle Scholar
  25. Miyanaga A, Funa N, Awakawa T, Horinouchi S (2008) Direct transfer of starter substrates from type I fatty acid synthase to type III polyketide synthases in phenolic lipid synthesis. Proc Natl Acad Sci U S A 105:871–876CrossRefGoogle Scholar
  26. Morant M, Jørgensen K, Schaller H, Pinot F, Møller BL, Werck-Reichhart D, Bak S (2007) CYP703 is an ancient cytochrome P450 in land plants catalyzing in-chain hydroxylation of lauric acid to provide building blocks for sporopollenin synthesis in pollen. Plant Cell 19:1473–1487CrossRefGoogle Scholar
  27. Nakano C, Funa N, Ohnishi Y, Horinouchi S (2012) The O-methyltransferase SrsB catalyzes the decarboxylative methylation of alkylresorcyclic acid during phenolic lipid biosynthesis by Streptomyces griseus. J Bacteriol 194:1544–1551CrossRefGoogle Scholar
  28. Pan Z, Rimando AM, Baerson SR, Fishbein M, Duke SO (2007) Functional characterization of desaturases involved in the formation of the terminal double bond of an unusual 16:3Δ9,12,15 fatty acid isolated from Sorghum bicolor root hairs. J Biol Chem 282:4326–4335CrossRefGoogle Scholar
  29. Posehn SE, Kim SY, Wee AGH, Suh DY (2012) Mapping the mechanism of the resorcinol ring formation catalyzed by ArsB, a type III polyketide synthase from Azotobacter vinelandii. Chembiochem 13:2212–2217CrossRefGoogle Scholar
  30. Quilichini TD, Grienenberger E, Douglas CJ (2015) The biosynthesis, composition and assembly of the outer pollen wall: a tough case to crack. Phytochemistry 113:170–182CrossRefGoogle Scholar
  31. Reusch RN, Sadoff HL (1983) Novel lipid components of the Azotobacter vinelandii cyst membrane. Nature 302:268–270CrossRefGoogle Scholar
  32. Satou R, Miyanaga A, Ozawa H, Funa N, Katsuyama Y, Miyazono KI, Tanokura M, Ohnishi Y, Horinouchi S (2013) Structural basis for cyclization specificity of two Azotobacter type III polyketide synthase: a single amino acid substitution reverses their cyclization specificity. J Biol Chem 288:34146–34157CrossRefGoogle Scholar
  33. Schöner TA, Kresovic D, Bode HB (2015) Biosynthesis and function of bacterial dialkylresorcinol compounds. Appl Microbiol Biotechnol 99:8323–8328CrossRefGoogle Scholar
  34. Smith S, Tsai SC (2007) The type I fatty acid and polyketide synthases: a tale of two megasynthases. Nat Prod Rep 24:1041–1072CrossRefGoogle Scholar
  35. Stasiuk M, Kozubek A (2010) Biological activity of phenolic lipids. Cell Mol Life Sci 67:841–860CrossRefGoogle Scholar
  36. Wallace KK, Zhao B, McArthur HAI, Reynolds KA (1995) In vivo analysis of straight-chain and branched-chain fatty acid biosynthesis in three actinomycetes. FEMS Microbiol Lett 131:227–234CrossRefGoogle Scholar

Copyright information

© Springer Nature Switzerland AG 2019

Authors and Affiliations

  1. 1.Department of ChemistryTokyo Institute of TechnologyTokyoJapan
  2. 2.Department of Biotechnology, Graduate School of Agricultural and Life SciencesThe University of TokyoTokyoJapan

Personalised recommendations